US3117147A - Organo-metal chelates of polyamino polyacetic acids - Google Patents

Organo-metal chelates of polyamino polyacetic acids Download PDF

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US3117147A
US3117147A US84773A US8477361A US3117147A US 3117147 A US3117147 A US 3117147A US 84773 A US84773 A US 84773A US 8477361 A US8477361 A US 8477361A US 3117147 A US3117147 A US 3117147A
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Horst G Langer
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Dow Chemical Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/22—Tin compounds
    • C07F7/2224—Compounds having one or more tin-oxygen linkages

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  • This invention relates to a new class of chemical compounds and to a method of their preparation, the compounds being characterized as organo metal salts of organo metal chelates of ethylene dinitrilo tetraacetic acid and polyamino polyacetic acids.
  • metal chelates are useful biologically in that the chelatcd metal provides a reservoir of that metal ion for the physiological system into which it is passed, or it can be exchanged for another metal in the system and thus be useful, for example, in detoxification operations.
  • the metal chelate added to a biological system also carry additional organo groups which can contribute to its usefulness without impairing biological activity or possibly while enhancing the biological activity of the compound.
  • organo tin compounds characterized by their being chelates of certain amino acids which chelates will also carry other organo metal groups rendering the compounds useful in organic systems.
  • This invention accordingly is embodied in a new kind of chemical compound which is a novel salt of fully substituted organo metal and may be characterized essentially as a salt of organo substituted metal formed with a chelating agent, wherein the chelating portion of the molecule is fully occupied by additional organo metal moiety. More specifically the structure of the composition may be shown in conventional fashion by the following representation:
  • R represents the organo constituents alike or different on the metal.
  • Me and Me represent the metal which could be the same or different, Me being chelates and Me being a part of the salt; and X represents the chelating moiety of the molecule; n is an integer which is large enough to satisfy the valence of Me m is an integer and is large enough to satisfy the X moiety; 0 may be 0, as when Me is divalent, but generally has a positive value which satisfies the valence of Me More specifically these compounds may take the form of his trivinyl tin salt of the diphenyl tin chelate of ethylene dinitrilo tetra acetic acid, which is represented by the following formula:
  • the organo substitution of the tin which is in the salt forming portion of molecule, may be an unsaturated group, such as a vinyl group, or further that the organo group of the tin atom may be a phenyl group, or it may be any other more or less reactive group.
  • tin carries both, i.e., unsaturated moieties in one position, the other moieties in the other.
  • the structure of the compounds leads to a number of advantages in that the points of variability introduce the possibility of making the compound very specific biologically, or very broadly active as an insecticide, bactericide, herbicide or parasiticide.
  • the compound offers so many sites for the inclusion of chemical moieties and combinations of moieties that tailor made specific insecticides become possible.
  • Typical compounds which can be made in accordance with this invention are the following:
  • organo metal portions of the compound is best exemplified by organo tin salts which are readily available commercially as hydroxides, halides, acetates or his organo oxides having at least the following in the strucan accurate indication of the manipulations involved in the formation of each compound.
  • N'CH2OI-Iz-N B-Hydroxyethyl ethylene diamine triacetic acid. /6 (3) Di ethylene triaminepentaaoetic acid.
  • the alkyl group rgam metal halide (hydroxide,oxide,aeetate) between the nitrogen atoms may be 2, 3 or 4 carbon "Referring back to the general formula and the specific 5 .group or the number (if mtmgens and groups may formulas 'for the trivinyl tin salt used as starting material l s so thiat h compougii cal ⁇ become in Example -I it is, of course, evident from the structure amine g g g Also g 3 that the raw materials necessary for the formation are, ace y y mxy pmxye o at least, the essential chielating agent, which in this inthe extent of one Per nitrogen atom stance was ethylenediaminetetraacetic acid and a trivinyl Inasmuch as the materials used are inherently reactive, tin compound.
  • the trivinyl tin salt temperature at which the reaction is carried out maybe portion of a molecule it is most advantageous to have as in the range which will keep. the materials in their liquid raw materials the corresponding tin hydroxide.
  • tin phase i.e. solutions. Since the reaction is carried out in hydroxide,--With the tinin the tetra valent form, the re- Water, temperature from approximately ambient to apmaining 3 valences of the tin being satisfied by Whatever 35 proaching 100 C. are suitable; as is true of most reacorgano group is to be carried by the compound, is the tions of this character elevated temperature causes the basic material used to react with ethylenediaminetetrareaction to go more quickly.
  • Me are selected from the group consisting of metal than the phenyl groups attached in this reaction'the coratoms from groups 4A, 5A, and 2B of the periodic classiresponding dialkyl tin compound or other organo metal ficatiornwhich are at least bivalent and may be the same; compound, is used as a starting material. It has a value one lessthan the valence of Me; m is an :Thus'the organo groups attached to the tin atoms in integer two less'than the valence of Me"; Me(R) -being the compound, as'described generally herein, may be any the chelated" metal portion of the molecule.
  • the bis (trivinyl tin) salt of the d-iphenly l tin 'chclate carry certain common substituents such as halogens, and of ethylenediaminetetraacctic acid. are substituted with a hydroxyl or ether groups.
  • Sirnilar- 3 The his (triphenyl tin) salt of the diphenyl ,tin 'ly Where I have used tin as illustrating the reactions spechelate of.ethylenediaminetetraacetic acid.
  • any metal having the corresponding level of 4 any metal having the corresponding level of 4;
  • the bis (tributyl tin) salt of the diphenyl tin chelate reactivity with organic moieties is useful for the purposes. of ethylenediaminetetraacetic acid.
  • the bis (trivinyl tin) salt of the diphenyl. lead periodic classification of elements may be used, namely, chelate of ethylenediarninetetraaceflic acid. lead, germanium, arsenic, antimony and mercury, in its 6.
  • the method of forming the tin (II) salt of the divinyl tin (IV) chelate of ethylene dlnitrilo tetraacetic acid which comprises reacting ethylene dinitrilo tetra-aoetic acid with divinyl tin (IV) oxide to form the divinyl tin (IV) chelate of ethylene dinitrilo tetraaoetic acid and thereafter reacting said chelate With stannous chloride to form the tin (II) salt of the divinyl tin (IV) chelate of ethylene dinitn'lo tetraacetic acid.
  • the method of fonning the 'his (trivinyl tin (IV)) salt of the mono tin (II) chelate of ethylene dinitrilo tetraacetic acid which comprises reacting ethylene d-indtrilo tetraacetic acid with tr-ivinyl tin (IV) hydroxide to form the his (trivinyl tin (IV)) salt of ethylene dinitrilo tetraacetic acid and thereafter reacting said salt with bi-functional stannous chloride to form the his (trivinyl tin (IV)) salt of the mono tin (II) chelate of ethylene dinitrilo tetraacetic acid.
  • the method of forming bis (trivinyl tin) salt of 6 the divinyl tin chelate of ethylenediamlinetetraacetic acid which comprises reacting trivinyl tin hydroxide with divinyl tin ehelate of ethylenediaminetetraacetic acid to form the his (tniv inyl tin) salt of the divinyl tin chelate of ethylenediaminetetraacetic acid.

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Description

United States Patent i Chemical Company, Midland, Mich, a corporation of Delaware N0 Drawing. Filed Jan. 25, 1961, Ser. No. 84,773 Claims. (Cl. 260-4295) This invention relates to a new class of chemical compounds and to a method of their preparation, the compounds being characterized as organo metal salts of organo metal chelates of ethylene dinitrilo tetraacetic acid and polyamino polyacetic acids.
For many purposes it is essential to have certain metals in organic form wherein the metal can be made available for its biological activity. For example for many pur poses metal chelates are useful biologically in that the chelatcd metal provides a reservoir of that metal ion for the physiological system into which it is passed, or it can be exchanged for another metal in the system and thus be useful, for example, in detoxification operations. In this connection reference may be had to United States Patent 2,698,823, Bersworth and Rubin. Quite often it is desirable that the metal chelate added to a biological system also carry additional organo groups which can contribute to its usefulness without impairing biological activity or possibly while enhancing the biological activity of the compound.
It is, accordingly, a fundamental object of this invention to provide organo tin compounds characterized by their being chelates of certain amino acids which chelates will also carry other organo metal groups rendering the compounds useful in organic systems.
It is another object of the invention to provide tetra substituted organo tin compounds carrying four functional groups any one of which may be modified to alter the properties of the tin compounds.
Other objects and advantages of the invention will in part be obvious'and in part appear hereinafter.
This invention accordingly is embodied in a new kind of chemical compound which is a novel salt of fully substituted organo metal and may be characterized essentially as a salt of organo substituted metal formed with a chelating agent, wherein the chelating portion of the molecule is fully occupied by additional organo metal moiety. More specifically the structure of the composition may be shown in conventional fashion by the following representation:
wherein the R represents the organo constituents alike or different on the metal. Me and Me represent the metal which could be the same or different, Me being chelates and Me being a part of the salt; and X represents the chelating moiety of the molecule; n is an integer which is large enough to satisfy the valence of Me m is an integer and is large enough to satisfy the X moiety; 0 may be 0, as when Me is divalent, but generally has a positive value which satisfies the valence of Me More specifically these compounds may take the form of his trivinyl tin salt of the diphenyl tin chelate of ethylene dinitrilo tetra acetic acid, which is represented by the following formula:
3,117,147 Patented Jan. 7, 1954 From the example it will be seen that the organo substitution of the tin, which is in the salt forming portion of molecule, may be an unsaturated group, such as a vinyl group, or further that the organo group of the tin atom may be a phenyl group, or it may be any other more or less reactive group. In the example given tin carries both, i.e., unsaturated moieties in one position, the other moieties in the other.
With a molecule of this structure it will be seen that functionality appears in several places and that it can take the form of unsaturation suitable for reaction with polymer forming materials, or for direct polymerization, and further the molecule can be used as the carrier of other groups.
The structure of the compounds leads to a number of advantages in that the points of variability introduce the possibility of making the compound very specific biologically, or very broadly active as an insecticide, bactericide, herbicide or parasiticide. The compound offers so many sites for the inclusion of chemical moieties and combinations of moieties that tailor made specific insecticides become possible.
Typical compounds which can be made in accordance with this invention are the following:
Bis (trivinyl tin) salt of the diphenyl tin chelate of EDTA Bis (triphenyl tin) salt of the diphenyl tin chelate of EDTA Bis (tributyl tin) salt of the diphenyl tin chelate of EDTA Bis (trivinyl tin) salt of the diphenyl lead chelate of EDTA Bis (trivinyl tin) salt of the tin (II) chelate of EDTA Tin (II) salt of the divinyl tin chelate of EDTA The organo metal portions of the compound is best exemplified by organo tin salts which are readily available commercially as hydroxides, halides, acetates or his organo oxides having at least the following in the strucan accurate indication of the manipulations involved in the formation of each compound.
Example I Bis-trivinyl tin salt of di-phenyl tin ethylenediaminetetraacetic acid. I
1 millimole of bis-trivinyl tin EDTA and 1 millimole of di-phenyl tin dichloride are slightly heated in milliliters of acetone. A few drops of water are added until the reactants are dissolved. By adding a large excessof Water, the compound precipitates, is filtered off and air dried.
II: Two millimoles of trivinyl tin hydroxide are added to 1 millimole of divinyl tin EDTA (chelate) in 100 ml. of 60 ethanol in Water. The reactants dissolve completely and after addition of excess ethanol the bis (trivinyl tin) salt of the divinyl tin chelate of EDTA precipitates. The crystals are filtered off and dried by suction.
III: One millimole of stannous chloride dissolved in a small volume of ethanol is added slowly to one millimole of the divinyl tin (IV) chelate of EDTA in approximately 100 ml. water. The pH is kept between 5 and 7 by addition of sodium hydroxide. The reactants dissolve completely and the tin (II) salt of the divinyl tin (IV) chelate of EDTA is precipitated through addition of ethanol.
IV: Substitution in Example III of the his (trivinyl tin 3 (IV)) salt of EDTA for the divinyl tin (IV) chelate of EDTA results in formation of the bis (trivinyl tin (IV)) salt of'the'monotin (II) chelate of EDTA.
The equations summarizing the preferred ways of mak- 4 Since it is reaction of these materials with a chelating agent which is described, it is apparent that the chelating portion of the reaction mixture may be an ethylenediaminetetraacetic acid as the "type compound but it is also ing the compounds as follows: 5 clear that the chelating agent may have a formula cor- O responding to the following: o1n=oH)3.snoi-om CH;iiO-Sn.(OH=GH2)a CHZCOOH l .HNG9 CH2 CH2 BNH 1|V (CHz),,-NCH2COOH 10 CHzCOOH ornooou h 9 e wherein 21 represents an integer 'hauing a valueof 2, 3 or 4, and b represents an integer having a value of 1, 2, 3 organo tin halide (hydroxide, oxide, acetate) (CGH5)2SI1(CD2 fg chelating agents useful invthe formation ofthis or type compound are:
HOOCTCH CE-QCOOH (l) Ethylene diarnine tetra acetic acid.
N'CH2OI-Iz-N (2) B-Hydroxyethyl ethylene diamine triacetic acid. /6 (3) Di ethylene triaminepentaaoetic acid.
I I (4) Tri ethylene tetraamine hexaracetic acid. (the B-hy 7 1' droxyethyl variants of 3 and 4 when the fl-hydroxyl G 6H5 C5115 group replaces an acid moiety).
(5) In compounds of this general class the alkyl group rgam metal halide (hydroxide,oxide,aeetate) between the nitrogen atomsmay be 2, 3 or 4 carbon "Referring back to the general formula and the specific 5 .group or the number (if mtmgens and groups may formulas 'for the trivinyl tin salt used as starting material l s so thiat h compougii cal} become in Example -I it is, of course, evident from the structure amine g g g Also g 3 that the raw materials necessary for the formation are, ace y y mxy pmxye o at least, the essential chielating agent, which in this inthe extent of one Per nitrogen atom stance was ethylenediaminetetraacetic acid and a trivinyl Inasmuch as the materials used are inherently reactive, tin compound. Specifically, to form the trivinyl tin salt temperature at which the reaction is carried out maybe portion of a molecule it is most advantageous to have as in the range which will keep. the materials in their liquid raw materials the corresponding tin hydroxide. Thus tin phase, i.e. solutions. Since the reaction is carried out in hydroxide,--With the tinin the tetra valent form, the re- Water, temperature from approximately ambient to apmaining 3 valences of the tin being satisfied by Whatever 35 proaching 100 C. are suitable; as is true of most reacorgano group is to be carried by the compound, is the tions of this character elevated temperature causes the basic material used to react with ethylenediaminetetrareaction to go more quickly. acetic acid. When this compound is reacted in an lappro- The compounds formed in accordance With the invenpriate stoichiometrtic amount, namely, 2 molm of tin for tion are colorless crystal solid, non h-ygroscopic comeach mole of.ethylenediarninetetraacetic acid, the mono- 4.0 pounds which may be reduced to line degrees of .subfunctional tin is attached to two acid groups of the ethyldivision and have considerable value as fungicides, slimienediarn'inetetraacetic acid. Tohave it carry more than cides, b actericides and insecticides. Testing indicates two tin atoms, it is reacted further with tri-organo tin complete activity against the southern ,armyworm in conhydroxide to a maximum extent of 4 moles per mole of oentrations of 50 parts per million and spotted spiderethylenediaminetetraacetic acid. This sequence of commites in concentrations of 500 parts per million. pounds is described in my copending application filed 'What is claimed is: contemporaneously herewith. 1. -A compound having a formula given by the, follow- When this di-tin salt is reacted With diphenyl tin diing:
Rn-Me'O 0 o OHZ-N -(GH N-- (CH2) .-N CHZC o oMe/Rn H20 CH2 llh 0= olyre'"-oi:=o JOOMeRH h chloride (or other di-organo tin di-halide, or other organo wherein a represents an integer having a value 111 the metal iii-halides, di-hydroxides), hydrogen chloride or range 2, 3, 4, and b represents an integer having a value H O is removed from the sphere of the reaction and the in the range 0-, 1, 2, 3; R moieties are selected from the bis trivinyl tin salt of diphenyl tin ethylenediarninetetragroup consisting of lower alkyl and phenyl moieties; Me acetic acid is formed. If it is'desired to have other groups and Me are selected from the group consisting of metal than the phenyl groups attached in this reaction'the coratoms from groups 4A, 5A, and 2B of the periodic classiresponding dialkyl tin compound or other organo metal ficatiornwhich are at least bivalent and may be the same; compound, is used as a starting material. It has a value one lessthan the valence of Me; m is an :Thus'the organo groups attached to the tin atoms in integer two less'than the valence of Me"; Me(R) -being the compound, as'described generally herein, may be any the chelated" metal portion of the molecule. alkyl or aryl'orgas'nic groups even Where those groups 2. The bis (trivinyl tin) salt of the d-iphenly l tin 'chclate carry certain common substituents such as halogens, and of ethylenediaminetetraacctic acid. are substituted with a hydroxyl or ether groups. Sirnilar- 3. The his (triphenyl tin) salt of the diphenyl ,tin 'ly Where I have used tin as illustrating the reactions spechelate of.ethylenediaminetetraacetic acid.
cifically, any metal having the corresponding level of 4; The bis (tributyl tin) salt of the diphenyl tin chelate reactivity with organic moietiesis useful for the purposes. of ethylenediaminetetraacetic acid.
For'exarnple, the other'rnletals of groups 4A, 5A, 2b. of 5. The bis (trivinyl tin) salt of the diphenyl. lead periodic classification of elements may be used, namely, chelate of ethylenediarninetetraaceflic acid. lead, germanium, arsenic, antimony and mercury, in its 6. The bis (trivin'yl tin) salt of the tin (II) chelate of divalent form, etc. ethylenediaminetetraacetic acid.
7. The tin (II) salt of the divinyl tin chelate of ethylenediaminetetraacetic acid.
8. The method of forming the tin (II) salt of the divinyl tin (IV) chelate of ethylene dlnitrilo tetraacetic acid which comprises reacting ethylene dinitrilo tetra-aoetic acid with divinyl tin (IV) oxide to form the divinyl tin (IV) chelate of ethylene dinitrilo tetraaoetic acid and thereafter reacting said chelate With stannous chloride to form the tin (II) salt of the divinyl tin (IV) chelate of ethylene dinitn'lo tetraacetic acid.
9. The method of fonning the 'his (trivinyl tin (IV)) salt of the mono tin (II) chelate of ethylene dinitrilo tetraacetic acid which comprises reacting ethylene d-indtrilo tetraacetic acid with tr-ivinyl tin (IV) hydroxide to form the his (trivinyl tin (IV)) salt of ethylene dinitrilo tetraacetic acid and thereafter reacting said salt with bi-functional stannous chloride to form the his (trivinyl tin (IV)) salt of the mono tin (II) chelate of ethylene dinitrilo tetraacetic acid.
10. The method of forming bis (trivinyl tin) salt of 6 the divinyl tin chelate of ethylenediamlinetetraacetic acid which comprises reacting trivinyl tin hydroxide with divinyl tin ehelate of ethylenediaminetetraacetic acid to form the his (tniv inyl tin) salt of the divinyl tin chelate of ethylenediaminetetraacetic acid.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES Martell, Chemistry of the Metal Ohelate Compounds, Prentice-Hall, Inc. (1952), pages 516, 536 to 542, and 598.

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3277132A (en) * 1962-06-13 1966-10-04 Wild Samuel Tin(ii) salts of orthophosphoric-mono-(beta-aminoethanol)ester
US3321361A (en) * 1964-04-06 1967-05-23 Stauffer Chemical Co Acaricidal method
US3321365A (en) * 1964-04-06 1967-05-23 Stauffer Chemical Co Acaricidal method

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB791119A (en) * 1954-09-08 1958-02-26 Pure Chem Ltd New organo-tin compounds
US2859104A (en) * 1952-10-02 1958-11-04 Geigy Chem Corp Ethylenediamine derivatives and preparation
US2965661A (en) * 1956-05-09 1960-12-20 Metal & Thermit Corp Vinylic tin compounds
US2997496A (en) * 1955-12-31 1961-08-22 Hoechst Ag Oxyalkylated organotin compounds and process for their preparation
US3016369A (en) * 1958-07-16 1962-01-09 Juan C Montermoso Organotin acrylic polymers

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2859104A (en) * 1952-10-02 1958-11-04 Geigy Chem Corp Ethylenediamine derivatives and preparation
GB791119A (en) * 1954-09-08 1958-02-26 Pure Chem Ltd New organo-tin compounds
US2997496A (en) * 1955-12-31 1961-08-22 Hoechst Ag Oxyalkylated organotin compounds and process for their preparation
US2965661A (en) * 1956-05-09 1960-12-20 Metal & Thermit Corp Vinylic tin compounds
US3016369A (en) * 1958-07-16 1962-01-09 Juan C Montermoso Organotin acrylic polymers

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3277132A (en) * 1962-06-13 1966-10-04 Wild Samuel Tin(ii) salts of orthophosphoric-mono-(beta-aminoethanol)ester
US3321361A (en) * 1964-04-06 1967-05-23 Stauffer Chemical Co Acaricidal method
US3321365A (en) * 1964-04-06 1967-05-23 Stauffer Chemical Co Acaricidal method

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